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6. Outsource to China

He attended the Los Angeles County High School for the Arts and then the San Francisco Art Institute. He took cooking classes, too, since he knew painting likely wouldn’t support him. “I thought I’d be a chef by night and paint by day,” he says. “Now I just have fabulous dinner parties.” The Yale School of Art pushed his thinking. There, Wiley devoured the whole academic buffet—art theory, world history, identity and cultural theory.

The question of identity wasn’t just academic. His father, Isiah Obot, had come from Nigeria in the seventies and studied architecture at UCLA, where he met Wiley’s mother. He left before Wiley was born, and Wiley’s mother destroyed all her pictures of him. “I always wanted to know what he looked like,” Wiley says. “As a portraitist, I was obsessed with his face.” (The name Wiley comes from his mother’s first husband.) When Wiley was 20, he raised $700 from family members, hopped a plane to Nigeria, and started searching. Knowing nothing more than his father’s name and expertise, he traveled to Akwa Ibom, the state in southern Nigeria where his father’s tribe originated, went to the state capital of Uyo, learned his father was working at a nearby university, and walked into the architecture department. “His name’s on the door,” Wiley says. “He’s the head of the department.”

It was awkward. “He didn’t understand my intention at first. He probably thought I was there to shake him down,” Wiley says. His father had recently married and hadn’t told his wife about his far-flung progeny. “I fell into this deep depression afterward.” He painted a series of portraits of his father. He had videotaped the whole saga and watched it over and over.

That was also around the time Wiley came out. The inciting incident: His girlfriend at the time came out to him. “I was like, ‘Well, if you’re not playing this game, I’m not playing either,’ ” he says. His brother wasn’t surprised. His mother was just happy she had five other kids who could give her grandchildren. His sisters? “Total fag hags,” Wiley says. Was there any trouble at school? “Art school? San Francisco? Get the fuck out of here. The problem was if you were straight.”

After graduating from Yale, Wiley took a residency at the Studio Museum in Harlem. “One Hundred Twenty-fifth Street was so dense and packed with pageantry and peacocking,” he says. “I wanted to try and get that down in painting.” He started stopping men on the street and asking to paint their portraits. Eventually he and his subjects started talking about art history, and Wiley began painting their portraits based on their favorite classics.

He didn’t have one big break so much as a string of them. In 2002, a couple of high-profile exhibitions at the Studio Museum featured his paintings. Jeffrey Deitch took notice and offered him his first major solo show. Wiley was on an Italian Renaissance kick and had the idea of creating his own Sistine Chapel. The result was Faux/Real, which featured guys in modern hip-hop garb posing as saints in front of swarms of sperm, among other decorative patterns, while other men floated among clouds like thugged-out angels on a canvas sky hung across the ceiling.

In Rumors of War (2005), he transposed men into contexts of military glory. Down (2008) depicted dead and dying men on a massive scale, while Black Light (2009) used blown-up photos instead of painted figures. The World Stage takes mostly black and brown men from Brazil, Senegal, Nigeria, India, and Israel and sets them against a country-specific backdrop, such as Dutch wax-­resist fabrics.

His next gallery show, called “Mr. President,” will feature portraits of presidents of various African countries as they wish to be portrayed, he says, and will address “notions of taste and vulgarity.” Painting a powerful political figure is different from pulling a kid off the streets, of course. “It’s redundant, almost,” he says. But as Wiley sees it, it’s not his job to judge. “The games I’m playing have much more to do with using the language of power and the vocabulary of power to construct new sentences,” Wiley says. “It’s about pointing to empire and control and domination and misogyny and all those social ills in the work, but it’s not necessarily taking a position. Oftentimes it’s actually embodying it.”